CN117088920B - Pt complex and application thereof in organic light-emitting device - Google Patents
Pt complex and application thereof in organic light-emitting device Download PDFInfo
- Publication number
- CN117088920B CN117088920B CN202311356945.2A CN202311356945A CN117088920B CN 117088920 B CN117088920 B CN 117088920B CN 202311356945 A CN202311356945 A CN 202311356945A CN 117088920 B CN117088920 B CN 117088920B
- Authority
- CN
- China
- Prior art keywords
- complex
- compound
- deuterium
- hydrogen
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000010410 layer Substances 0.000 claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 31
- 239000002346 layers by function Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims description 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- -1 aryl silane Chemical compound 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 1
- 230000005693 optoelectronics Effects 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000003993 interaction Effects 0.000 abstract description 4
- 230000005540 biological transmission Effects 0.000 abstract description 3
- 238000012856 packing Methods 0.000 abstract description 3
- 230000000171 quenching effect Effects 0.000 abstract description 3
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 62
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000001819 mass spectrum Methods 0.000 description 37
- 238000005259 measurement Methods 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 37
- 239000012467 final product Substances 0.000 description 31
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 27
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 18
- 229940125904 compound 1 Drugs 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 238000002390 rotary evaporation Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002386 leaching Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 3
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 3
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 3
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 3
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 description 3
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 3
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 3
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 3
- MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 3
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 3
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 3
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 3
- QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 3
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 3
- 229960003805 amantadine Drugs 0.000 description 3
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229940125797 compound 12 Drugs 0.000 description 3
- 229940125758 compound 15 Drugs 0.000 description 3
- 229940126086 compound 21 Drugs 0.000 description 3
- 229940126208 compound 22 Drugs 0.000 description 3
- 229940125961 compound 24 Drugs 0.000 description 3
- 229940125878 compound 36 Drugs 0.000 description 3
- 229940126545 compound 53 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- FDBYIYFVSAHJLY-UHFFFAOYSA-N resmetirom Chemical compound N1C(=O)C(C(C)C)=CC(OC=2C(=CC(=CC=2Cl)N2C(NC(=O)C(C#N)=N2)=O)Cl)=N1 FDBYIYFVSAHJLY-UHFFFAOYSA-N 0.000 description 3
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 2
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011365 complex material Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000005309 thioalkoxy group Chemical group 0.000 description 2
- 125000004953 trihalomethyl group Chemical group 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- NOODRYARAKMAEM-UHFFFAOYSA-N benzonitrile;platinum(2+) Chemical compound [Pt+2].N#CC1=CC=CC=C1.N#CC1=CC=CC=C1 NOODRYARAKMAEM-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- VMFMUJZRXZXYAH-UHFFFAOYSA-N n-[5-[[5-chloro-4-[2-[2-(dimethylamino)-2-oxoacetyl]anilino]pyrimidin-2-yl]amino]-4-methoxy-2-(4-methylpiperazin-1-yl)phenyl]prop-2-enamide Chemical compound C=CC(=O)NC=1C=C(NC=2N=C(NC=3C(=CC=CC=3)C(=O)C(=O)N(C)C)C(Cl)=CN=2)C(OC)=CC=1N1CCN(C)CC1 VMFMUJZRXZXYAH-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to the technical field of organic photoelectric material preparation, in particular to a Pt complex and application thereof in an organic light-emitting device. The Pt complex provided by the invention has very low efficiency roll-off, by introducing the triphenylsilicon large steric hindrance group, the close packing among planar Pt complex molecules is effectively reduced, the luminescence quenching effect caused by the interaction among luminescent molecules is inhibited, the energy transmission between a host material and a guest material is effectively improved, and the device efficiency is further improved. So that the Pt complex has a very low roll-off efficiency. The Pt complex is used as a functional layer, particularly used as a light-emitting layer to manufacture an organic electroluminescent device, the current efficiency is improved, the lighting voltage is reduced, the service life of the device is greatly prolonged, and the energy is effectively transferred to the Pt complex for light emission instead of heat after most electrons and holes are combined.
Description
Technical Field
The invention relates to the technical field of organic photoelectric material preparation, in particular to a Pt complex and application thereof in an organic light-emitting device.
Background
With the development of multimedia technology and the improvement of informatization requirements, the requirements on the performance of panel displays are higher and higher. The OLED has a series of advantages of autonomous luminescence, low-voltage direct current drive, full solidification, wide viewing angle, rich colors and the like, and is widely paid attention to potential application in a new-generation display and illumination technology, so that the OLED has a very wide application prospect. The organic electroluminescent device is a spontaneous luminescent device, and the mechanism of OLED luminescence is that electrons and holes are respectively injected from positive and negative poles and then migrate, recombine and decay in an organic material under the action of an external electric field to generate luminescence. Typical structures of OLEDs include one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer, and a light emitting layer. Although the research progress of organic electroluminescence is very rapid, there are still many problems to be solved, and the green Pt complex with high efficiency and long lifetime has been a problem to be solved by those skilled in the art.
Disclosure of Invention
The invention aims at overcoming the defects of the prior art and provides a Pt complex and application thereof in an organic light-emitting device. By introducing the triphenylsilicon large steric hindrance group, the close packing between planar Pt complex molecules is effectively reduced, the luminescence quenching effect caused by interaction between luminescent molecules is inhibited, the energy transmission between a host material and a guest material is effectively improved, and the concentration of high-energy excitons in a luminescent layer is reduced, so that the green light material with high efficiency and long service life is realized. Such Pt complexes therefore find important application in organic light emitting devices.
In order to achieve the purpose of the invention, the technical scheme of the invention is as follows:
according to one or more embodiments, the present invention provides a Pt complex having a structure represented by formula I:
in the formula I, the ring A is selected from five-membered ring, five-membered heterocycle, six-membered ring or condensed ring, wherein hetero atom is nitrogen atom, oxygen atom or sulfur atom;
said R is 1 、R 2 、R 3 、R 4 Each independently of the others is a single substituent up to the maximum number of substitutions possibleA group or no substituent, any adjacent substituents optionally joined or fused to form a ring; r is R 1 、R 2 、R 3 、R 4 Each independently selected from the group consisting of hydrogen (H), deuterium (D), C1-C24 alkyl, C1-C24 deuterated alkyl, substituted or unsubstituted C3-C24 cycloalkyl, substituted or unsubstituted C6-C30 aryl, C6-C30 aza-aryl, C6-C30 aryl-silane, and; r is R 4 Can form a condensed ring with the ring A where the condensed ring is positioned by sharing the ring edge.
In some embodiments of the compounds, in formula I, the R 1 Selected from C1-C10 alkyl, C3-C10 cycloalkyl, R 2 、R 3 、R 4 Each independently selected from the group consisting of hydrogen, deuterium, C1-C10 alkyl, C1-C10 deuterated alkyl, C3-C10 cycloalkyl, C6-C18 aryl, and combinations thereof.
R 4 Selected from the group consisting of hydrogen, deuterium, C1-C10 alkyl, C1-C10 deuterated alkyl, C3-C10 cycloalkyl, C6-C18 aryl, C6-C18 aza-aryl, C18-C30 aryl silane, and combinations thereof.
In some embodiments of the compounds, ring a in formula I is selected from furyl, thienyl, benzofuryl, benzothienyl, phenyl ring, fluorenyl, N-heterofluorenyl, spirofluorenyl.
In some embodiments of the compounds, R in formula I 1 Selected from hydrogen, deuterium, t-butyl or amantadine.
R 2 Selected from the group consisting of hydrogen, deuterium, t-butyl, amantadine, phenyl, biphenyl, and combinations thereof.
R 3 Selected from the group consisting of hydrogen, deuterium, t-butyl, phenyl, biphenyl, and combinations thereof.
R 4 Selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, butyl, t-butyl, pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, amantadine, phenyl, biphenyl, fluorenyl, N-heterofluorenyl, pyridinyl, triarylsilane, and combinations thereof.
As a preference, R in formula I 1 -R 4 The hydrogen atoms in the radicals may be partially deuterated or fully deuterated, R in formula I 1 -R 4 ArbitraryAdjacent two substituents are not linked or are linked to each other to form a ring structure.
According to one or more embodiments, the Pt complex is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:
in another aspect, the invention also provides application of the Pt complex with the general structure shown in the formula I in preparation of an electronic device.
Further, the electronic device includes an organic photovoltaic device, an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field quench device (O-FQD), a light emitting electrochemical cell (LEC), and an organic laser diode (O-laser).
Alternatively, pt complexes of the general structure shown in formula I above are used as light emitting layer materials for electronic devices.
In another aspect, the present invention also provides an organic electroluminescent device comprising a cathode, an anode, and at least one organic functional layer therebetween; the organic functional layer comprises a Pt complex with a general structure shown in the formula I.
Further, the organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises a Pt complex with a general structure shown in the formula I. The mass percentage of the Pt complex is 0.1% -50%.
In another aspect, the invention also provides an organic photoelectric device, a substrate layer and a first electrode; a second electrode facing the first electrode; and a luminescent material layer disposed between the first electrode and the second electrode; wherein the luminescent material layer comprises Pt complex with the general structure shown in the formula I. For example, the Pt complex may be included as a dopant in the light emitting material layer.
The invention also provides a composition, which comprises the Pt complex with the general structure shown in the formula I.
The invention also provides a preparation comprising the Pt complex with the general structure shown in the formula I or the composition and at least one solvent. The solvent is not particularly limited, and for example, an unsaturated hydrocarbon solvent such as toluene, xylene, mesitylene, tetrahydronaphthalene, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, a halogenated saturated hydrocarbon solvent such as carbon tetrachloride, chloroform, methylene chloride, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, a halogenated unsaturated hydrocarbon solvent such as chlorobenzene, dichlorobenzene, trichlorobenzene, an ether solvent such as tetrahydrofuran, tetrahydropyran, an ester solvent such as an alkyl benzoate, and the like, which are known to those skilled in the art, can be used.
The invention also provides a display or lighting device comprising one or more of the organic electroluminescent devices as described above.
Compared with the prior art, the invention has the beneficial effects that:
the Pt complex provided by the invention has very low efficiency roll-off, by introducing the triphenylsilicon large steric hindrance group, the close packing among planar Pt complex molecules is effectively reduced, the luminescence quenching effect caused by the interaction among luminescent molecules is inhibited, the energy transmission between a host material and a guest material is effectively improved, and the device efficiency is further improved. So that the Pt complex has a very low roll-off efficiency. The Pt complex is used as a functional layer, particularly used as a light-emitting layer to manufacture an organic electroluminescent device, the current efficiency is improved, the lighting voltage is reduced, the service life of the device is greatly prolonged, and the energy is effectively transferred to the Pt complex for light emission instead of heat after most electrons and holes are combined.
Detailed Description
The following describes the present invention in detail. The following description of the constituent elements may be based on the representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. The present disclosure may be understood more readily by reference to the following detailed description and the examples included therein. Before the present compounds, devices and/or methods are disclosed and described, it is to be understood that, unless otherwise indicated, they are not limited to specific synthetic methods or specific reagents as such may vary. It is also to be understood that the terminology used herein is for the purpose of describing particular aspects only and is not intended to be limiting. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing, the exemplary methods and materials are now described.
"C1-C24 alkyl" as used herein refers to monovalent alkyl groups having 1 to 24 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms. Examples of this term are: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, n-hexyl and the like.
"cycloalkyl" as used herein for C3-C24 refers to a cyclic alkyl group having 3 to 14 carbon atoms and having a single or multiple ring fused, optionally substituted with 1 to 3 alkyl groups. Such cycloalkyl groups include, for example, a single ring structure such as cyclopropyl, cyclobutyl, cyclopentyl, cyclooctyl, 1-methylcyclopropyl, and 2-methylcyclopentyl, 2-methylcyclooctyl, etc., or a multiple ring structure such as adamantyl, etc.
As used herein, "C6-C30 aryl" refers to an unsaturated aromatic carbocyclic ring having 6 to 30 carbon atoms and having a single ring (e.g., phenyl) or a multiple ring fused (e.g., naphthyl or anthracenyl). Preferred aryl groups include phenyl, naphthyl, and the like. Unless otherwise defined for the individual substituents, such aryl groups may be optionally substituted with 1 to 3 of the following substituents: hydroxy, acyl, acyloxy, alkyl, alkoxy, alkenyl, alkynyl, amino, aminoacyl, aryl, aryloxy, carboxyl ester, aminocarboxyl ester, cyano, halogen, nitro, heteroaryl, heterocycle, thioalkoxy, trihalomethyl, and the like. Preferred substituents include alkyl, alkoxy, halogen, cyano, nitro, trihalomethyl and thioalkoxy. But is not limited thereto.
The "heterocycle" as used herein refers to a generic term for groups in which one or more carbons in the ring are replaced by heteroatoms including, but not limited to, oxygen, sulfur or nitrogen atoms, and the heterocycle may be a monocyclic heterocarbyl, monocyclic heteroaryl, fused heterocarbyl or fused heterocarbyl, examples of which may include, but are not limited to, pyridyl, pyrrolyl, pyridyl, thienyl, furyl, indolyl, quinolinyl, isoquinolinyl, benzothienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, and the like.
As used in this specification and the appended claims, the singular forms "a," "an," and "the" include plural referents unless the context clearly dictates otherwise. Thus, for example, reference to "a component" includes a mixture of two or more components.
Unless otherwise indicated, all commercial reagents referred to in the following experiments were used directly after purchase.
In a preferred embodiment of the present invention, the OLED device of the present invention comprises a hole transporting layer, and the hole transporting material may preferably be selected from known or unknown materials, particularly preferably from the following structures, but does not represent that the present invention is limited to the following structures (Ph is phenyl):
in a preferred embodiment of the present invention, the hole injection layer is comprised in the OLED device of the present invention. The preferred hole injection layer materials of the present invention are of the following structure, but do not represent the invention as limited to the following structure:
in a preferred embodiment of the present invention, the electron transport layer may be selected from at least one of the following compounds, but does not represent the present invention limited to the following structures:
the OLED device of the present invention contains a host material, which may be selected from known or unknown materials, particularly preferably selected from the following structures, but does not represent the limitation of the present invention to the following structures:
the preparation method of the Pt complex, i.e., the guest compound, and the light emitting performance of the device are explained in detail in connection with the following examples.
EXAMPLE 1 Synthesis of Compound 1
Synthesis of Compounds 1-3: compound 1-1 (290 mg,1 mmoL) and compound 1-2 (178 mg,1 mmoL) were dissolved in 50 mL toluene solution. 10 mL aqueous sodium carbonate (2M) and tetrakis (triphenylphosphine) palladium (57 mg,0.05 mmoL) were added under nitrogen. After the reaction system was refluxed for 48 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:1, to give product 1-3 (150 mg, yield 43%). Mass spectrum m/z, theory 345.11; actual measurement value M+H:346.14.
synthesis of Compounds 1-5: compounds 1-3 (345 mg,1 mmoL) and compounds 1-4 (205 mg,1 mmoL) were dissolved in 50 mL anhydrous toluene solution. Sodium tert-butoxide (192 mg,2 mmoL), palladium acetate (12 mg,0.05 mmoL) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmoL) were added under nitrogen atmosphere. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:1, product 1-5 (212 mg, 45% yield) was obtained. Mass spectrum m/z, theory 470.37; actual measurement value M+H:471.39.
synthesis of Compounds 1-7: compounds 1 to 5 (470 mg,1 mmoL) and compounds 1 to 6 (283 mg,1 mmoL) were dissolved in 50 mL anhydrous toluene solution. Sodium tert-butoxide (192 mg,2 mmoL), palladium acetate (12 mg,0.05 mmoL) and tri-tert-butylphosphine tetrafluoroborate (145 mg,0.5 mmoL) were added under nitrogen atmosphere. The reaction system was refluxed for 72 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 2:1, to give product 1-7 (230 mg, yield 37%). Mass spectrum m/z, theory 625.30; actual measurement value M+H:626.32.
synthesis of Compounds 1-8: buLi (0.5 mL,1 mmoL,2M in hexane) was slowly added to a solution of compounds 1-7 (625 mg,1 mmoL) in tetrahydrofuran (50 mL) at-78deg.C. After 3 hours of reaction, trimethyltin chloride (1 mL,1 mmoL,1M in Hexane) was slowly added. After slowly warming to room temperature, the reaction was allowed to proceed overnight, then allowed to react at 80℃for 6 hours. After cooling to room temperature, ice water 1 mL was added. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the crude product obtained was directly used for the next reaction.
Synthesis of Compounds 1-10: compounds 1 to 8 (711 mg,1 mmoL) and compounds 1 to 9 (282 mg,1 mmoL) were dissolved in 50 mL toluene solution. Tetrakis (triphenylphosphine) palladium (57 mg,0.05 mmoL) was added under nitrogen. After the reaction system was refluxed for 48 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:1, to give the product 1-10 (450 mg, yield 64%). Mass spectrum m/z, theory 701.33; actual measurement value M+H:702.35.
synthesis of Compounds 1-11: buLi (0.5 mL,1 mmoL,2M in hexane) was slowly added to a solution of compounds 1-10 (701 mg,1 mmoL) in tetrahydrofuran (50 mL) at-78deg.C. After 3 hours of reaction, triphenylchlorosilane (294 mg,1 mmoL) was slowly added. After slowly warming to room temperature, the reaction was allowed to proceed overnight, then allowed to react at 80℃for 6 hours. After cooling to room temperature, ice water 1 mL was added. The solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:2, to give the product 1-11 (467 mg, yield 53%). Mass spectrum m/z, theory 881.51; actual measurement value M+H:882.53.
synthesis of Compound 1: compounds 1-11 (882 mg,1 mmoL) and the compound bis (benzonitrile) platinum (II) (472 mg,1 mmoL) were dissolved in 50 mL benzonitrile solution. Under the condition of nitrogen atmosphere, the temperature is raised to 180 ℃ for reaction for 48 hours. After cooling to room temperature, the solvent was removed by rotary evaporation and the residue was extracted with dichloromethane (3×100 mL). The organic phase is washed with water and dried over sodium sulfate. The solvent is removed by reduced pressure distillation, the crude product is separated and purified by a silica gel chromatographic column, and the leaching agent is as follows: dichloromethane: petroleum ether = 1:2 to give product 1 (230 mg, yield 21%). Mass spectrum m/z, theory 1074.46; actual measurement value M+H:1075.48.
example 2: synthesis of Compound 6
Compound 6 was synthesized referring to the synthetic route of compound 1. The yield of the final product was 26%. Mass spectrum m/z, theory 1286.62; actual measurement value M+H:1287.64.
example 3: synthesis of Compound 9
Compound 9 was synthesized referring to the synthetic route of compound 1. The yield of the final product was 23%. Mass spectrum m/z, theory 1246.49; actual measurement value M+H:1247.51.
example 4: synthesis of Compound 12
Compound 12 was synthesized referring to the synthetic route of compound 1. The yield of the final product was 22%. Mass spectrum m/z, theory 1202.43; actual measurement value M+H:1203.45.
example 5: synthesis of Compound 15
Referring to the synthetic route for compound 1, compound 15 was synthesized. The yield of the final product was 27%. Mass spectrum m/z, theory 1104.41; actual measurement value M+H:1105.43.
example 6: synthesis of Compound 21
Compound 21 was synthesized referring to the synthetic route of compound 1. The yield of the final product was 24%. Mass spectrum m/z, theory 1194.46; actual measurement value M+H:1195.48.
example 7: synthesis of Compound 22
Compound 22 was synthesized by reference to the synthetic route of compound 1. The yield of the final product was 21%. Mass spectrum m/z, theory 1236.51; actual measurement value M+H:1237.53.
example 8: synthesis of Compound 24
Compound 24 was synthesized referring to the synthetic route for compound 1. The yield of the final product was 31%. Mass spectrum m/z, theory 1210.49; actual measurement value M+H:1211.52.
example 9: synthesis of Compound 36
Referring to the synthetic route for compound 1, compound 36 was synthesized. The yield of the final product was 27%. Mass spectrum m/z, theory 1239.43; actual measurement value M+H:1240.45.
example 10: synthesis of Compound 44
Compound 44 was synthesized referring to the synthetic route of compound 1. The yield of the final product was 25%. Mass spectrum m/z, theory 1206.55; actual measurement value M+H:1207.57.
example 11: synthesis of Compound 45
Compound 45 was synthesized referring to the synthetic route for compound 1. The yield of the final product was 24%. Mass spectrum m/z, theory 1246.49; actual measurement value M+H:1247.52.
example 12: synthesis of Compound 48
Compound 48 was synthesized referring to the synthetic route for compound 1. The yield of the final product was 26%. Mass spectrum m/z, theory 1202.43; actual measurement value M+H:1203.45.
example 13: synthesis of Compound 53
Compound 53 was synthesized referring to the synthetic route of compound 1. The yield of the final product was 29%. Mass spectrum m/z, theory 1210.49; actual measurement value M+H:1211.52.
example 14: synthesis of Compound 61
Compound 61 was synthesized referring to the synthetic route for compound 1. The yield of the final product was 23%. Mass spectrum m/z, theory 1166.43; actual measurement value M+H:1167.45.
example 15: synthesis of Compound 65
Compound 65 was synthesized referring to the synthetic route for compound 1. The yield of the final product was 22%. Mass spectrum m/z, theory 1200.41; actual measurement value M+H:1201.43.
example 16: synthesis of Compound 74
Compound 74 was synthesized referring to the synthetic route of compound 1. The yield of the final product was 26%. Mass spectrum m/z, theory 1230.46; actual measurement value M+H:1231.48.
example 17: synthesis of Compound 78
Referring to the synthetic route for compound 1, compound 78 was synthesized. The yield of the final product was 35%. Mass spectrum m/z, theory 1230.46; actual measurement value M+H:1231.48.
example 18: synthesis of Compound 79
Referring to the synthetic route for compound 1, compound 79 was synthesized. The yield of the final product was 32%. Mass spectrum m/z, theory 1256.48; actual measurement value M+H:1257.51.
example 19: synthesis of Compound 81
Referring to the synthetic route for compound 1, compound 81 was synthesized. The yield of the final product was 25%. Mass spectrum m/z, theory 1160.48; actual measurement value M+H:1161.51.
example 20: synthesis of Compound 84
Referring to the synthetic route for compound 1, compound 84 was synthesized. The yield of the final product was 21%. Mass spectrum m/z, theory 1160.48; actual measurement value M+H:1161.50.
example 21: synthesis of Compound 85
Referring to the synthetic route for compound 1, compound 85 was synthesized. The yield of the final product was 30%. Mass spectrum m/z, theory 1226.43; actual measurement value M+H:1227.45.
example 22: synthesis of Compound 89
Referring to the synthetic route for compound 1, compound 89 was synthesized. The yield of the final product was 31%. Mass spectrum m/z, theory 1210.45; actual measurement value M+H:1211.47.
example 23: synthesis of Compound 92
Compound 92 was synthesized by reference to the synthetic route of compound 1. The yield of the final product was 27%. Mass spectrum m/z, theory 1206.37; actual measurement value M+H:1207.39.
example 24: synthesis of Compound 96
Referring to the synthetic route for compound 1, compound 96 was synthesized. The yield of the final product was 23%. Mass spectrum m/z, theory 1190.39; actual measurement value M+H:1191.41.
example 25: synthesis of Compound 97
Compound 97 was synthesized referring to the synthetic route for compound 1. The yield of the final product was 28%. Mass spectrum m/z, theory 1188.50; actual measurement value M+H:1189.52.
example 26: synthesis of Compound 99
Referring to the synthetic route for compound 1, compound 99 was synthesized. The yield of the final product was 23%. Mass spectrum m/z, theory 1246.49; actual measurement value M+H:1247.51.
example 27: synthesis of Compound 105
Compound 105 was synthesized referring to the synthetic route of compound 1. The yield of the final product was 22%. Mass spectrum m/z, theory 1208.46; actual measurement value M+H:1209.48.
example 28: synthesis of Compound 110
Referring to the synthetic route for compound 1, compound 110 was synthesized. The yield of the final product was 28%. Mass spectrum m/z, theory 1218.40; actual measurement value M+H:1219.42.
example 29: synthesis of Compound 114
Compound 114 was synthesized with reference to the synthetic route of compound 1. The yield of the final product was 24%. Mass spectrum m/z, theory 1211.49; actual measurement value M+H:1212.51.
example 30: synthesis of Compound 118
Compound 118 was synthesized by reference to the synthetic route of compound 1. The yield of the final product was 24%. Mass spectrum m/z, theory 1257.47; actual measurement value M+H:1258.49.
example 31: synthesis of Compound 133
Referring to the synthetic route for compound 1, compound 133 was synthesized. The yield of the final product was 29%. Mass spectrum m/z, theory 1122.44; actual measurement value M+H:1123.46.
example 32: synthesis of Compound 137
Referring to the synthetic route for compound 1, compound 137 was synthesized. The yield of the final product was 26%. Mass spectrum m/z, theory 1208.47; actual measurement value M+H:1209.49.
manufacturing of OLED device:
as a reference preparation mode of an embodiment of a device, the invention comprises evaporating p-doped material on the surface or anode of ITO glass with the size of 2 mm multiplied by 2 mm of light-emitting area, or co-evaporating the p-doped material with a hole-transporting material at a concentration of 1% -50% to form a Hole Injection Layer (HIL) of 5-100 nm, forming a hole-transporting layer (HTL) of 5-200 nm on the hole injection layer, then co-evaporating a host material and a Pt complex (guest material) prepared by the invention at a volume ratio of 97:3 to form a light-emitting layer (EML) of 10-100nm, finally co-evaporating to form an electron-transporting layer (ETL) of 35 nm, and evaporating a cathode Al 70 nm, thereby manufacturing the organic electroluminescent diode.
In a preferred embodiment, the structure of the bottom-emitting OLED device provided by the present invention is: the glass containing ITO is used as an anode, and HIL is HT-1:P-3 (95:5, v/v%) and the thickness is 10 nanometers; HTL is HT-1 and has a thickness of 90 nanometers; EBL is HT-8, the thickness is 10 nanometers, EML is host material (H-9): compound 1 (97:3, v/v%) provided by the invention, the thickness is 35 nanometers, ETL is ET-3: liQ (50:50, v/v%) was 35 nm thick, and then an organic electroluminescent diode was prepared by evaporating 70 nm of cathode Al, which was designated as application example 1.
Referring to the method provided in application example 1, the prepared compound 6, compound 9, compound 12, compound 15, compound 21, compound 22, compound 24, compound 36, compound 44, compound 45, compound 48, compound 53, compound 61, compound 65, compound 74, compound 78, compound 79, compound 81, compound 84, compound 85, compound 89, compound 92, compound 96, compound 97, compound 99, compound 105, compound 110, compound 114, compound 118, compound 133 and compound 137 were used as the implementation object to replace compound 1, and a light-emitting layer was formed by co-evaporation with a host material compound at a volume ratio of 3:97, which was denoted as application examples 2 to 32.
Production of comparative example 1
Comparative example 1 was prepared with reference to the method provided in application example 1 described above, except that Pt-1 was used as the guest material of the light emitting layer in comparative example 1 instead of the Pt complex of the present invention. The chemical structure of compound Pt-1 in the comparative example is as follows:
the characteristics of the device examples and comparative examples prepared above, such as current efficiency, voltage and lifetime, were tested by standard methods, and the device luminescence characteristic data are shown in table 1.
TABLE 1 light emission characteristics data sheet for devices
As can be seen from table 1, compared with comparative example 1, application examples 1 to 32 exhibited good device performance in terms of both current efficiency and lifetime, and the improvement in the performance of each device application example was based on the Pt complex material of the present invention having a better ability to suppress the interaction between light-emitting molecules, and further, the Pt complex material was used as a host material for a light-emitting layer to prepare an electronic device having higher current efficiency and lifetime while reducing the driving voltage. The Pt complex provided by the invention has certain commercial application value.
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention.
Claims (10)
1. A Pt complex, characterized in that the Pt complex has a structure represented by the following formula I:
in the formula I, the ring A is selected from benzofuranyl, benzothienyl, benzene ring, fluorenyl, N-heterofluorenyl and spirofluorenyl; the R is 1 、R 2 、R 3 、R 4 Each independently is a single substituent to the maximum number of substituents possible or no substituents, R 1 Selected from hydrogen, deuterium, C1-C10 alkyl, C3-C10 cycloalkyl; r is R 2 、R 3 Each independently selected from hydrogen, deuterium, C1-C10 alkyl, C1-C10 deuterated alkyl, C3-C10 cycloalkyl, C6-C18 aryl; the R is 4 Selected from hydrogen, deuterium, C1-C10 alkyl, C1-C10 deuterated alkyl, C3-C10 cycloalkyl, C6-C18 aryl, C6-C18 aza-aryl, C18-C30 aryl silane.
2. The Pt complex of claim 1, wherein R in formula I 1 Selected from hydrogen, deuterium, tert-butyl or adamantyl; r is R 2 Selected from hydrogen, deuterium, tertiary butyl, adamantyl, phenyl, biphenyl; r is R 3 Selected from hydrogen, deuterium, tert-butyl, phenyl, biphenyl.
3. The Pt complex of claim 1, wherein R 4 Selected from hydrogen, deuterium, methyl, ethyl, propyl, butyl, tert-butyl, pentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, fluorenyl, N-heterofluorenyl, pyridinyl.
4. A Pt complex, characterized in that the Pt complex is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:
5. use of a Pt complex according to any one of claims 1-4 in the manufacture of an electronic device.
6. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises a cathode, an anode and at least one organic functional layer interposed therebetween; the Pt complex according to any one of claims 1 to 4 is contained in the organic functional layer.
7. An organic optoelectronic device, comprising: a substrate layer, a first electrode; a second electrode facing the first electrode; and a luminescent material layer disposed between the first electrode and the second electrode; wherein the luminescent material layer comprises the Pt complex according to any one of claims 1 to 4.
8. A composition comprising the Pt complex of any one of claims 1-4.
9. A formulation comprising the Pt complex of any one of claims 1-4 and at least one solvent.
10. A display or lighting device comprising one or more of the organic electroluminescent devices of claim 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311356945.2A CN117088920B (en) | 2023-10-19 | 2023-10-19 | Pt complex and application thereof in organic light-emitting device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311356945.2A CN117088920B (en) | 2023-10-19 | 2023-10-19 | Pt complex and application thereof in organic light-emitting device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN117088920A CN117088920A (en) | 2023-11-21 |
| CN117088920B true CN117088920B (en) | 2024-01-23 |
Family
ID=88770200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311356945.2A Active CN117088920B (en) | 2023-10-19 | 2023-10-19 | Pt complex and application thereof in organic light-emitting device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117088920B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118290488B (en) * | 2024-04-16 | 2024-09-17 | 浙江华显光电科技有限公司 | Pt complex and application thereof in organic light-emitting device |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20120038056A (en) * | 2010-10-13 | 2012-04-23 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| JP2013544759A (en) * | 2010-09-20 | 2013-12-19 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Novel organic electroluminescent compound and organic electroluminescent device using the same |
| CN105409021A (en) * | 2013-07-29 | 2016-03-16 | 默克专利有限公司 | Electroluminescence device |
| CN108640950A (en) * | 2018-06-05 | 2018-10-12 | 长春海谱润斯科技有限公司 | A kind of iridium metals organic coordination compound and its organic luminescent device |
| CN108822155A (en) * | 2018-06-05 | 2018-11-16 | 长春海谱润斯科技有限公司 | It is a kind of miscellaneous with iridium complex and its organic luminescent device |
| WO2022164086A1 (en) * | 2021-01-28 | 2022-08-04 | 주식회사 랩토 | Organometallic complex and organic electroluminescent device comprising same |
| CN116496308A (en) * | 2023-04-07 | 2023-07-28 | 浙江华显光电科技有限公司 | Condensed cyclic compound and organic light-emitting device comprising the same |
-
2023
- 2023-10-19 CN CN202311356945.2A patent/CN117088920B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013544759A (en) * | 2010-09-20 | 2013-12-19 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Novel organic electroluminescent compound and organic electroluminescent device using the same |
| KR20120038056A (en) * | 2010-10-13 | 2012-04-23 | 롬엔드하스전자재료코리아유한회사 | Novel compounds for organic electronic material and organic electroluminescent device using the same |
| CN105409021A (en) * | 2013-07-29 | 2016-03-16 | 默克专利有限公司 | Electroluminescence device |
| CN108640950A (en) * | 2018-06-05 | 2018-10-12 | 长春海谱润斯科技有限公司 | A kind of iridium metals organic coordination compound and its organic luminescent device |
| CN108822155A (en) * | 2018-06-05 | 2018-11-16 | 长春海谱润斯科技有限公司 | It is a kind of miscellaneous with iridium complex and its organic luminescent device |
| WO2022164086A1 (en) * | 2021-01-28 | 2022-08-04 | 주식회사 랩토 | Organometallic complex and organic electroluminescent device comprising same |
| CN116496308A (en) * | 2023-04-07 | 2023-07-28 | 浙江华显光电科技有限公司 | Condensed cyclic compound and organic light-emitting device comprising the same |
Non-Patent Citations (1)
| Title |
|---|
| 圆偏振热活化延迟荧光材料及其器件的研究进展;杨晓东 等;《有机化学》;第43卷;第1292-1309页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN117088920A (en) | 2023-11-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN116217608B (en) | Silicon-containing compounds and their use in organic light-emitting devices | |
| CN116514859B (en) | Narrow-emission luminescent compound and application thereof in electronic device | |
| CN116874517B (en) | Selenophene-containing compound and application thereof in organic light-emitting device | |
| CN108929234B (en) | Aromatic amine derivative and organic electroluminescent device thereof | |
| CN117088920B (en) | Pt complex and application thereof in organic light-emitting device | |
| CN118307502B (en) | Organic compound, OLED (organic light-emitting diode) with organic compound and organic light-emitting device | |
| CN118221640B (en) | Organic compound, OLED (organic light-emitting diode) with organic compound and organic light-emitting device | |
| CN116496308A (en) | Condensed cyclic compound and organic light-emitting device comprising the same | |
| WO2023093094A1 (en) | Organic electroluminescent device and display apparatus | |
| CN117209461B (en) | Organic photoelectric compound, composition with same and organic light-emitting device | |
| CN112125812B (en) | Compound and application thereof and device containing compound | |
| Zhang et al. | Triphenyl phosphine oxide-bridged bipolar host materials for green and red phosphorescent organic light-emitting diodes | |
| CN111725413A (en) | Organic electroluminescent device and display apparatus | |
| Braveenth et al. | Fluorene core with several modification by using donor type triphenylamine and carbazole derivatives for organic light emitting diodes | |
| CN115353483B (en) | Compound containing biscarbazole structure and organic electroluminescent device | |
| CN114605389B (en) | Thermal activation delay fluorescent material and device thereof | |
| CN113831332B (en) | Nitrogen-containing heterocyclic derivative and application thereof in organic electroluminescent device | |
| CN118290488B (en) | Pt complex and application thereof in organic light-emitting device | |
| CN115275072A (en) | Organic light-emitting device | |
| CN117229328B (en) | Pt complex with spirofluorene structure and application thereof in organic light-emitting device | |
| CN118239970B (en) | Boron nitride compound, organic electroluminescent device and application | |
| CN117946146B (en) | Boron-nitrogen compound containing imidazole and derivative group, organic electroluminescent device and application | |
| CN116903651B (en) | Selenium-containing luminescent compound and application thereof in electronic device | |
| Tang et al. | Novel tri-carbazole modified fluorene host material for highly efficient solution-processed blue and green electrophosphorescent devices | |
| CN118480064A (en) | Boron-nitrogen compound containing imidazole and derivative group, organic electroluminescent device and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |